General Strategies for the Asymmetric Synthesis of Oxygenated Natural Products

Abstract

Several years ago we initiated a program that was directed toward the design and development of general strategies that could be expeditiously applied to the formulation of concise, total syntheses of enantiomerically pure, oxygenated natural products. Some targets of considerable interest and obvious importance in this regard include: KDO (3 deoxy-D-manno-octulopyranosate) (1), which is a higher monosaccharide found in the cell wall of Gram-negative bacteria;1,2 the antibiotic tirandamycin A (2) as well as its degradation product tirandamycic acid (3);3,4 Prelog-Djerassi lactone (4), which is obtained from the degradation of several macrolide antibiotics including methymycin (5);5,6other medicinally important macrolide antibiotics such as the erythromycins A (6) and B (7);5,7 and the ansa antibiotics macbecin (8) and herbimycin A (9), which are potential anticancer agents.8,9

Keywords

Boron Adduct Hydride Cerium Lactone

Recipient of a National Institutes of Health (National Cancer Institute) Research Career Development Award (1980–1985).